Broader, Greener, and More Efficient: Recent Advances in Asymmetric Transfer Hydrogenation

被引:408
作者
Wang, Chao [1 ]
Wu, Xiaofeng [1 ]
Xiao, Jianliang [1 ]
机构
[1] Univ Liverpool, Liverpool Ctr Mat & Catalysis, Dept Chem, Liverpool L69 7ZD, Merseyside, England
关键词
asymmetric catalysis; green chemistry; homogenous catalysis; hydrogenation; organocatalysis;
D O I
10.1002/asia.200800196
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric transfer hydrogenation has become a practically useful tool in reduction chemistry in the last decade or so. This was largely triggered by the seminal work of Noyori and co-workers in the mid-1990s and is driven by its complementing chemistry to hydrogenation employing H-2. This Focus Review attempts to present a "holistic" overview on the advances in the area, focusing on the achievements recorded around the last three years. These include more-efficient and "greener" metal catalysts, catalysts that enable hydrogenation as well as transfer hydrogenation, biomimetic and organocatalysts, and their applications in the reduction of C=O, C=N, and C=C bonds. Also highlighted are efforts in the development of environmentally benign and reusable catalytic systems.
引用
收藏
页码:1750 / 1770
页数:21
相关论文
共 293 条
[1]   Mechanism of the hydrogenation of ketones catalyzed by trans-dihydrido(diamine)ruthenium(II) complexes [J].
Abdur-Rashid, K ;
Clapham, SE ;
Hadzovic, A ;
Harvey, JN ;
Lough, AJ ;
Morris, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) :15104-15118
[2]   RuHCl(diphosphine)(diamine): Catalyst precursors for the stereoselective hydrogenation of ketones and imines [J].
Abdur-Rashid, K ;
Lough, AJ ;
Morris, RH .
ORGANOMETALLICS, 2001, 20 (06) :1047-1049
[3]   Ruthenium dihydride RuH2(PPh3)2((R,R)-cyclohexyldiamine) and ruthenium monohydride RuHCl(PPh3)2((R,R)-cyclohexyldiamine):: Active catalyst and catalyst precursor for the hydrogenation of ketones and imines [J].
Abdur-Rashid, K ;
Lough, AJ ;
Morris, RH .
ORGANOMETALLICS, 2000, 19 (14) :2655-2657
[4]   Catalytic cycle for the asymmetric hydrogenation of prochiral ketones to chiral alcohols:: Direct hydride and proton transfer from chiral catalysts trans-Ru(H)2(diphosphine)(diamine) to ketones and direct addition of dihydrogen to the resulting hydridoamido complexes [J].
Abdur-Rashid, K ;
Faatz, M ;
Lough, AJ ;
Morris, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) :7473-7474
[5]   A simple and efficient catalyst system for the asymmetric transfer hydrogenation of ketones [J].
Ahlford, Katrin ;
Zaitsev, Alexey B. ;
Ekstrm, Jesper ;
Adolfsson, Hans .
SYNLETT, 2007, (16) :2541-2544
[6]   New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].
Ahrendt, KA ;
Borths, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244
[7]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[8]   Recent progress in chiral Bronsted acid catalysis [J].
Akiyama, Takahiko ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010
[9]   Ru(arene)(amino alcohol)-catalyzed transfer hydrogenation of ketones: Mechanism and origin of enantioselectivity [J].
Alonso, DA ;
Brandt, P ;
Nordin, SJM ;
Andersson, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9580-9588
[10]   2-azanorbornyl alcohols: Very efficient ligands for ruthenium-catalyzed asymmetric transfer hydrogenation of aromatic ketones [J].
Alonso, DA ;
Nordin, SJM ;
Roth, P ;
Tarnai, T ;
Andersson, PG ;
Thommen, M ;
Pittelkow, U .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3116-3122